23386-17-6

Upstream product

• 4654-39-1 4-bromophenethanol 
• 98-07-7 Benzotrichlorid 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 104-10-9 2-(4'-aminophenyl)ethyl alcohol 

Downstream Products

• 64008-48-6 4-(4-Bromo-phenyl)-2-(2,4-dichloro-phenyl)-butyric acid methyl ester 
• 1238799-75-1 2-(4-bromophenyl)ethyl-1-S-triisopropylsilylsulfide 
• 67595-65-7 1-(4'-Bromphenyl)-ethyl-kation 

Relevant academic research and scientific papers

Organocatalytic Chlorination of Alcohols by P(III)/P(V) Redox Cycling

A catalytic system for the chlorination of alcohols under Appel conditions was developed. Benzotrichloride is used as a cheap and readily available chlorinating agent in combination with trioctylphosphane as the catalyst and phenylsilane as the terminal reductant. The reaction has several advantages over other variants of the Appel reaction, e.g., no additional solvent is required and the phosphane reagent is used only in catalytic amounts. In total, 27 different primary, secondary, and tertiary alkyl chlorides were synthesized in yields up to 95%. Under optimized conditions, it was also possible to convert epoxides and an oxetane to the dichlorinated products.

Gallium-catalyzed reductive chlorination of carboxylic acids with copper(II) chloride

Described herein is the direct chlorination of carboxylic acids using copper(II) chloride via a gallium(III)-catalyzed reduction in the presence of a hydrosiloxane. During this reductive chlorination, the counteranions of CuCl2 functioned as a chloride source.

The direct anti-Markovnikov addition of mineral acids to styrenes

The direct anti-Markovnikov addition of strong Bronsted acids to alkenes remains an unsolved problem in synthetic chemistry. Here, we report an efficient organic photoredox catalyst system for the addition of HCl, HF and also phosphoric and sulfonic acids to alkenes, with complete regioselectivity. These transformations were developed using a photoredox catalyst in conjunction with a redox-active hydrogen atom donor. The nucleophile counterion plays a critical role by ensuring high reactivity, with 2,6-lutidinium salts typically furnishing the best results. The nature of the redox-active hydrogen atom donor is also consequential, with 4-methoxythiophenol providing the best reactivity when 2,6-lutidinium salts are used. A novel acridinium sensitizer provides enhanced reactivity within several of the more challenging reaction manifolds. This Article demonstrates how nucleophilic addition reactions mediated by photoredox catalysis can change the way electrophilic and homofugal precursors are constructed.

A divergent synthesis of oligoarylalkanethiols with Lewis-basic N-donor termini

Araliphatic thiols are key molecules for the formation of self-assembled monolayers with high long-range order. If these monolayers shall act as bases for the attachment of other molecules, the respective thiols need to carry suitable functional groups, such as the amino or the pyridine group. Due to their Lewis-basicity, these groups are not compatible with the thiol group under most reaction conditions. Here, an entry into this versatile class of compounds is presented, by using fundamental building blocks in which the thiol groups are protected as triisopropylsilyl sulfides making them compatible with many reagents including Grignard reagents and palladium catalysts. With this strategy at hand, six thiols with bi- and terphenyl backbones, one to three methylene groups, and amino or pyridine head groups became accessible in short reaction sequences. The Royal Society of Chemistry 2010.

Lithiophenylalkyllithiums: New dilithium reagents having both sp2- and sp3-hybridised remote carbanionic centres

The reaction of chloro-(2-chloroethyl)benzenes (1), 4-chloro-(3-chloropropyl)benzene (3) or 4-chlorophenyl chloromethyl ether (5) with lithium power using naphthalene as the electron shuttle (8 mol%) in the presence of different carbonyl compounds [Busub